One-Pot Synthesis of 3,4-Dihydrocoumarins via C-H Oxidation/Conjugate Addition/Cyclization Cascade Reaction

被引:1
|
作者
Kim, Dae Young [1 ]
机构
[1] Soonchunhyang Univ, Dept Chem, Asan 31538, Chungnam, South Korea
来源
MOLECULES | 2023年 / 28卷 / 19期
基金
新加坡国家研究基金会;
关键词
organocatalysis; one-pot reaction; ortho-quinone methides; dihydrocoumarins; oxazolones; ORTHO-QUINONE METHIDES; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL DIHYDROCOUMARINS; CYCLOADDITIONS; DERIVATIVES; ALKYLATION; ALDEHYDES; ACCESS; ROUTE;
D O I
10.3390/molecules28196853
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 3,4-dihydrocoumarin derivatives were obtained from 2-alkyl phenols and oxazolones via C-H oxidation and cyclization cascade in the presence of silver oxide (Ag2O) and p-toluenesulfonic acid as a Bronsted acid catalyst. This approach provides a one-pot strategy to synthesize the multisubstituted 3,4-dihydrocoumarins with moderate to high yields (64-81%) and excellent diastereoselectivity (>20:1).
引用
收藏
页数:11
相关论文
共 50 条
  • [21] Enantioselective one-pot synthesis of 2-amino-4H-chromenes via C-H oxidation and Michael addition/ring closure sequences
    Kim, Kyeong Seop
    Kim, Dae Young
    SYNTHETIC COMMUNICATIONS, 2022, 52 (02) : 291 - 299
  • [22] A one-pot process for synthesis of eight-membered cyclopalladated amidines via cascade C-H activation and insertion
    Xu, Fen
    Song, Yuan-Yuan
    Zhou, Hui-Min
    Liu, Chun-Sen
    Lu, Ya-Zhou
    Du, Jun-Ping
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 924
  • [23] Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade
    Zhu, Dong-Xing
    Liu, Jian-Guo
    Xu, Ming-Hua
    Journal of the American Chemical Society, 2021, 143 (23): : 8583 - 8589
  • [24] Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade
    Zhu, Dong-Xing
    Liu, Jian-Guo
    Xu, Ming-Hua
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (23) : 8583 - 8589
  • [25] Synthesis of diverse heterocycles via one-pot cascade cross-dehydrogenative-coupling ( CDC)/cyclization reaction
    Zhang, Chao
    Li, Tianlei
    Wang, Liguo
    Rao, Yu
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (03): : 386 - 391
  • [26] Diastereoselective intramolecular cyclization/Povarov reaction cascade for the one-pot synthesis of polycyclic quinolines
    Kuznetsova, E. A.
    Smolobochkin, A., V
    Rizbayeva, T. S.
    Gazizov, A. S.
    Voronina, J. K.
    Lodochnikova, O. A.
    Gerasimova, D. P.
    Dobrynin, A. B.
    Syakaev, V. V.
    Shurpik, D. N.
    Stoikov, I. I.
    Burilov, A. R.
    Pudovik, M. A.
    Sinyashin, O. G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (28) : 5515 - 5519
  • [27] Synthesis of Isoxazoles via One-Pot Oxidation/Cyclization Sequence from Propargylamines
    Duan, Mengyan
    Hou, Guodong
    Zhao, Yabiao
    Zhu, Congjun
    Song, Chuanjun
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 11222 - 11225
  • [28] One-pot Synthesis of Oxindoles through C-H Alkylation and Intramolecular Cyclization of Azobenzenes with Internal Olefins
    Han, Sang Hoon
    Mishra, Neeraj Kumar
    Jo, Hyeim
    Oh, Yongguk
    Jeon, Mijin
    Kim, Saegun
    Kim, Woo Jung
    Lee, Jong Suk
    Kim, Hyung Sik
    Kim, In Su
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2396 - 2401
  • [29] Synthesis of Natural Product-like Polyheterocycles via One-Pot Cascade Oximation, C-H Activation, and Alkyne Annulation
    Zheng, Liyao
    Bin, Yunhui
    Wang, Yunpeng
    Hua, Ruimao
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 8911 - 8919
  • [30] One-pot synthesis of indenobenzofurans via tandem Michael addition-elimination and palladium-catalysed C-H activation
    Naik, Vijaykumar
    Khan, Faiz Ahmed
    ARKIVOC, 2022, : 66 - 80